Oakland Vacations from $131

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Your Oakland Vacation

From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.

The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
Wyndham Grand Pittsburgh Downtown
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Kimpton Hotel Monaco Pittsburgh by IHG
Hilton Garden Inn Pittsburgh Airport

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland

Oakland Hotel Deals

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Aug 24 to Aug 25
$148 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (405 reviews)
"Conveniently located, very friendly and helpful staff, comfortable beds (uncomfortable sofa bed!), Internet access good. The restaurant could have more variety of options"

Reviewed on Aug 16, 2025

Courtyard by Marriott Pittsburgh University Center
Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive, Pittsburgh, PA
Fully refundable
$127 nightly
The price is $145 total per night from Aug 24 to Aug 25
$145 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Great room, terrific bar staff, convenient to University. We had a great time!"

Reviewed on Aug 10, 2025

Hotel Indigo Pittsburgh University-Oakland by IHG
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Aug 31 to Sep 1
$214 total
Aug 31 - Sep 1
Total includes taxes and fees
9.2/10 Wonderful! (676 reviews)
"I travel quite a bit but this one really impressed me!"

Reviewed on Aug 16, 2025

The Oaklander Hotel, Autograph Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Oakland

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.